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Photograph: WASIO photography
West Loop
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This sexy eatery was the first to brave Randolph Street back when it was, er, a little less gentrified. Many, many years later, the food still holds up (and the place is still as date-worthy as it was when Harry met Sally). Golden housemade gnocchi is doused in a creamy, earthy truffle sauce; tuna fillet is dressed up with a lively combo of balsamic and mint; and the pistachio gelato with merengue and hot fudge is utterly unshareable. If you are looking for something to share, pop a bottle of bubbly out on the sidewalk patio and lament about the strip’s good old days.

Venue name: Vivo
Address: 838 W Randolph St

Cross street: between Green and Peoria Sts
Opening hours: Lunch (Mon–Fri), dinner
Transport: El stop: Green, Pink to Clinton. Bus: 8, 20.
Price: Average main course: $22
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